Holiday rentals in Pineland

Sunny Sanibel - Gorgeous Loggerhead Walkout Unit

Loggerhead Cay 351 is a fantastic ground floor walk out condo residence in the sought after Loggerhead Cay development of Sanibel`s East End. "Sunny Sanibel" features two spacious bedrooms and bathrooms, a fully equipped kitchen, direct Gulf views, and a walk out patio, this residence is both beautiful and functional! With resort grade amenities including tennis, pickleball, Olympic sized heated swimming pool, shuffleboard, and community grills, guests will surely return year after year!

Vacation in Cape Coral in direct sea situation.

Villa Pleasure - enjoy cosy days in the beautiful villa, with a fantastic view directly on the Honeymoon Lake. The south facing Villa Pleasure offers comfortable accommodation for a maximum of 8 guests in 4 bedrooms in northwest Cape Coral. The Villa is brightly decorated and decorated with attention to detail. Outside there is a heated pool (with salt water technology) with plenty of privacy and a barbecue grill and sun loungers that invite you to sunbathe. Children up to 6 years free.

2/2 Home in Bokeelia, Boat Lift Included!

This two level 2 bedroom, 2 bathroom canal front home is exactly what's needed for an excellent vacation on beautiful Pine Island! This property has beautiful tropical décor to get you settled into the island lifestyle. You can relax and enjoy the views and wildlife on the back patio or grill the day's catch. This canal has incredible Gulf access and you will be out to the intra-coastal in minutes for some of the best fishing in not just the country, but the world. Bring your boat!

Waterfront Oasis with Boat Lift & Hot Tub

Bask in endless sun at our Jugg Creek canal-front home, a stone's throw from Charlotte Harbor and iconic islands like Captiva and Boca Grande. Dive into 'Old Florida' with unspoiled beaches and cute eateries. Watch dolphins from your doorstep and savor rainbow sunsets. Our beautiful cottage boasts a outdoor hot tub and shower, screened in porch, grill, and kayaks with a kayak launch right on the dock. Docking is on us, with a new dock & 10k pound boat lift available April-December.

Bokeelia Golf Retreat

Welcome to BOKEELIA GOLF, a modern and stylish vacation retreat located in the popular Bokeelia, FL. This renovated house features a contemporary modern style with 6-beds, 4-Baths, an inviting open-concept living, dining area, IN/OUT kitchen, pool & play game room. Quiet neighborhood with free parking and a spacious yard featuring a BBQ for family enjoyment. Bokeelia Golf seamlessly combines a Golf Campus & Marina, creating an ideal setting for both golf and fishing enthusiasts.

Peaceful Lakeview Retreat / Screened Porch & Bikes

Escape to a peaceful lakeview retreat on Pine Island. Relax on the breezy screened porch, unwind in the cozy living room, and enjoy two serene bedrooms with smart TVs and comfortable bedding. The home features modern bathrooms, a fully stocked kitchen, fast Wi-Fi, and in-unit laundry for convenience. Pet-friendly and close to trails, marinas, and seafood spots — perfect for birdwatching, biking, fishing, or simply soaking up the island’s quiet charm and natural beauty.

Historic Boca Grande: 2 Bedroom Flat:#6 Special Rt

We made it through Milton and Helene and are ready to host you! A great, second floor, 2 bedroom, one bath flat in the heart of historic Boca Grande on the gorgeous Gasparilla Island. Across the street from The Temp Restaurant, and down the block from Hudson's Market. Going to the beach, no worries, it is just down the road. Just a 3 minute walk to the Gasparilla Inn. Guests receive a 10% discount on golf cart and bike rentals through Gasparilla Adventures.

KayoSun |10 Ppl|Heated Pool |Gym |Games|30minBeach

Enjoy the perfect mix of style, comfort, and value in sunny Cape Coral. Why book with us? Charming 2,000 ft² home 30 min to beaches, parks & golf Private heated pool Home gym Game room Fast Wi-Fi Fully equipped kitchen Work-from-home desk FREE onsite parking BBQ + outdoor dining Washer & dryer Family & kid-friendly Pool towels included Board & card games Easy self check-in Pet-friendly Fully fenced yard Spacious backyard Quiet neighborhood Modern, new build

Pine Island Pelican Suite: privacy, pool, gardens

Welcome to the Pelican Suite! Secure, private entrance, king bed, outdoor kitchen and patio. This suite is separate from the upstairs main house. Adults only. King bed, ensuite private bathroom with shower; AC. WiFi, cable, TV. Exclusive use of ground floor screened guest lanai: kitchen, fridge, BBQ. Beautiful gardens, small/secluded heated pool. Free parking. The Pelican Suite is ideal for a relaxing no-stress break in the sun!

BRAND NEW Luxury Villa w/Heated and Chilled Pool

Brand new high-end 3 bedroom 3 bath designer home, elegantly decorated with incredible views and direct no-bridge Gulf access. Come and make your lifetime memories in this elegantly appointed executive villa. Located near Matlacha, Sanibel, Fort Myers, and Naples. Extra wide canal with only trees opposite, a salt water lagoon, and just off the spreader canal means incredible solitude and privacy in your elegant oasis retreat.

Bokeelia Charming Island House

Welcome to your getaway home- a newly remodeled 2 bed 1 bath house, the first floor of a 2 unit duplex. Quiet and peaceful setting, enjoy one of the most natural reserved islands of Southwest Florida. Catch the ferry for a beach daytrip to famous nearby islands of Cayo Costa & Captiva or visit local art galleries and shops in nearby Matlacha. Perfect for biking, kayaking, fishing, sightseeing, etc.

Grande View - Large 3/3 Island Lakehouse w/Pool

Lakefront 3BR/3BA home in Bokeelia near Pineland! Enjoy island vibes with a heated pool, large screened lanai, and spacious open living area. Relax by the water, watch sunsets, or explore nearby marinas, beaches, and restaurants. Perfect for families or couples seeking a peaceful island escape with modern comfort and classic Florida charm.